19 Comfy, Casual & Chic Winter Outfits to Keep You Warm This Season

Here, I’m going to talk you through 19 comfy and casual winter outfits. I love effortless and timeless style, but I’m not fond of the cold. Finding the perfect balance between keeping warm and looking chic is something I’ve worked on for many years, and now I think I’ve got it spot on.

Cashmere sweater in black & cream for winter

1. Cashmere

One surefire way of staying stylish in winter is to invest in some cashmere. I went for a cashmere sweater with black and cream stripes, and a roll neck to protect me from the wind.

I’ve kept it classic with black cords and a wool coat for another layer. 

Casual winter outfit with a knit jacket

2. Knit jacket

This jacket has a timeless, Parisian style that feels up to date at the same time. Though it’s an easy one to dress up, for casual winter days, I’ve been styling it like this.

It’s a bit of a high-low approach that contrasts with the laid-back vibe of my knit.

Wearing menswear-inspired shapes in winter

3. Menswear shapes

Here, I’m wearing a gorgeous zip jumper. I couldn’t resist the shade, and the chunky knit in a menswear-inspired shape really suits my style. I’ve paired it with tailored trousers to smarten up the look. 

Layered winter outfit with a wrap coat

4. Wrap coat

To get the balance between chic, comfortable, and warm just right, my method comes down to layers.

There is something understatedly sexy about being wrapped up in a gorgeous coat, so you can easily make the look work in your favor.

Casual winter outfit with an oversized jacket

5. Oversized jacket

Something that has proved surprising wearable in my capsule wardrobe is this super-toasty wool jacket.

I love the oversized shape and the high collar. A splash of this season’s winter green is the icing on the cake.

I style it with Breton stripes for casual days, and the color really pops when I wear it against black. 

Comfy winter outfit with a tailored coat

6. Tailored coat

A go-to winter look for me is a great pair of jeans and a jumper. An easy way to make that outfit more stylish would be to add a tailored coat over the top.

I’ve opted for a timeless camel trench. My other layers are keeping me warm, so I tend to choose my coat with looks like this from an aesthetic point of view, rather than practical reasons. 

Classy winter outfit with skinny jeans

7. Skinny jeans

This is the kind of look that I would wear to a Christmas party. Skinny jeans because, on-trend or not, they make my legs look longer. I wear heels for the same reason.

I’ve styled them with a simple striped shirt and blazer to finish. 

Casual winter outfit contrasted with a coat

8. Contrast

Quite the opposite now and very much my daytime chic look, keeping things simple with jeans and a cotton shirt.

When I’m opting for comfort, which I am here with my Nikes on my feet, I like the contrast of a beautiful winter coat over the top. It instantly makes my super-chilled outfit feel more put together.

Fall-to-winter dress outfit

9. Fall dress for winter

There’s no reason why you can’t reach for autumnal dresses in winter; it’s just a matter of playing with the styling and adding a few more layers to make it work.

Here, I’m wearing a dress with no sleeves, but I’m not put off wearing it whatever the weather. I’ve been styling it with one of my favorite wool blazers, tights, and little black ankle boots. 

All-white tonal winter outfit

10. Tonal outfits

A little tonal love for you now. You can look chic and timeless very easily this winter by wearing variations of a similar tone.

It doesn’t have to be white, you could opt for camel or burgundy if that’s your cup of tea. 

Casual winter outfit for warmer climates

11. Blouse, blazer & flats

Milder winters warrant fewer layers, so those of you in warmer climates can get away with a blouse and a blazer at this time of year.

I’ve had a lot of wear out of these pointed-toe ballet flats; they’re so comfy it’s like wearing slippers.

How to dress well in winter

12. Light-colored blazer

Here, I’ve paired jeans with a simple cashmere crew neck for a classic go-to outfit.

I’ve finished the outfit with a gorgeous blazer, the shade lifts the tone of my whole outfit and the texture adds more depth to something that otherwise would be quite plain. 

Chic winter outfit in tones of gray

13. Shades of gray

Another tonal mix now, but not quite as exaggerated as my white version. This time I’ve opted for more of a subtle approach, integrating different shades of gray into my outfit idea.

If you look at everything I’m wearing as individual pieces, you’ll notice that they’re all pretty classic and timeless items.

When styled together, they become a melting pot of effortless style meets comfy winter days.

Winter outfit with ankle boots

14. Light-wash jeans

Even more casual now but hopefully no less chic. Here I’ve styled beige ankle boots with my cashmere jumper and straight-fit light wash jeans finished with a cream coat.

Comfy and casual winter white outfit

15. Winter whites

Winter whites again, this time styling a lovely wool blend pair of pleated trousers.

On my top half, I’m wearing a cashmere rollneck that I sized up to a medium to get that oversized fit and my faithful double-breasted coat to finish. 

Winter outfit in camel tones

16. Camel tones

Of course, my love of camel tones needed to sneak in somewhere. This cardigan is one of the most versatile pieces of knitwear I own.

I wear it as a cardigan, back to front as a jumper, knotted at the front to definite my waist, tucked in, half-tucked, and left open with a casual tee. There are so many ideas with just this one piece.

Comfy winter outfit with a backward cardigan

17. Wearing a cardigan backwards

Back to my favorite flats, but this time styling them with smarter tailored trousers for a little more polish. I’m wearing one of my knits back to front as a jumper.

How to wear a cardigan backwards

I like the understated sexiness of seeing a touch of skin at the back, though that dip to the first button is definitely high enough to get away with a bra underneath. 

Parisian-inspired winter outfit

18. Parisian style

Here I’m wearing a stunning, one-of-a-kind buttoned navy velvet jacket.

It feels a little bit Parisian, perhaps with a sprinkle of bohemian spirit, and styled with causal jeans and ankle boots make it stand out even more. 

Comfy & casual winter outfit with a coat

19. Wintergreen

Back to my wintergreen coat, but this time sharing how lovely that tone looks against camel shades. It feels rich and sumptuous, and the mix of textures adds interest.

I’ve styled them with my gray wash straight jeans and a lovely tanned tote.

Comfy & casual winter outfits

I really hope you’ve enjoyed my 19 chic and comfy winter outfits. Let me know which was your favorite look in the comments below.

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